You know nothing, Wil Wheaton.
That is not how you win elections. Elections are decided by about 3% of the eligible, that’s it. Take out everyone that don’t even bother to register, take out the people who don’t bother showing up (like all those outraged protestors in Portland that didn’t vote but decided to protest the outcome anyway), and, take out everyone that consistently votes for one party or the other.
Those “progressive” voters? You’re not going to “lose” them because they will always vote Democrat, just like the mass of voters who always vote Republican. Both groups can be dismissed, you don’t need to do ANYTHING to get them to vote a particular way.
To win an election, you focus on trying to get those swing voters to vote your way. It comes down to trying to convince 1.5% +1 of those voters to vote for your candidate. Trump did that with targeted advertising and a message that appealed to both people that could go either way, and people that haven’t shown up to vote lately. That rarely works, but Obama was able to do it and so was Trump. There is no way that Hillary was going to do that. If anything, as a candidate she was instrumental in making sure the “sometimes” voters on the Democrat side sat home and didn’t bother.